Winter Garden/Oakland Homes with Storage Exterior Features

Winter Garden/Oakland Homes with Storage Exterior Features

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where charm meets modern living in a picturesque setting. Nestled just a few miles west of Orlando, this vibrant community is renowned for its lush landscapes, historic downtown area, and a family-friendly atmosphere that makes it a sought-after destination for homebuyers.

Winter Garden, with its rich agricultural history, boasts a delightful mix of old-world charm and contemporary amenities. The historic downtown area features a variety of quaint shops, delightful cafes, and a thriving farmers’ market that brings the community together every Saturday. Just a stone's throw away, Oakland offers a serene, small-town vibe with beautiful parks and scenic trails that invite outdoor enthusiasts to explore the natural beauty of Central Florida.

When it comes to finding your dream home in this charming region, you’ll be pleased to discover a variety of properties that cater to every lifestyle. Many homes in Winter Garden and Oakland come equipped with exceptional storage exterior features, ensuring that your belongings are neatly organized and easily accessible. From spacious garages and outdoor sheds to cleverly designed storage solutions, these homes provide the perfect blend of functionality and style.

Whether you’re looking for a cozy bungalow or a spacious family home, the Winter Garden and Oakland area offers a wealth of options that cater to your needs. Experience the perfect fusion of community spirit and modern convenience in this delightful corner of Florida, where your dream home awaits!

Newest Winter Garden/Oakland Homes with Storage Exterior Features

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code

Experience the perfect blend of comfort, charm, and functionality in this beautiful Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story loft and a versatile fourth bedroom with its own half bath—perfect for guests, a media room, or flexible living space. The thoughtfully designed first floor features a private primary suite with an ensuite bath, two additional bedrooms sharing a full bath, a spacious family room, and a beautifully appointed kitchen that truly serves as the heart of the home. Kitchen features include built-ins and French doors that open to a gorgeous deck, creating an ideal setting for indoor/outdoor entertaining. A formal dining room and separate office with French doors provide additional space and privacy. Step outside to enjoy peaceful outdoor living in the landscaped backyard, complete with a private patio/deck perfect for relaxing or entertaining. A 2-car garage plus a dedicated golf cart garage adds exceptional convenience and storage. Located in highly sought-after Downtown Winter Garden, this home is close to top-rated schools, shopping, parks, West Orange Trail, and popular dining destinations. Enjoy the unique lifestyle of a golf-cart-friendly downtown district while being just minutes from everything you need. ON-SITE Generator for Hurricane season too. Recent updates include a New Roof (2023), New hot water tank, New mini-split, A/C Main (2023), and fresh interior paint (2026). Come discover all this wonderful home has to offer and make it yours!

502 Palm Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Harbor SubDv. ⋅ 34787 Zip Code

A rare opportunity in downtown Winter Garden awaits! This beautifully maintained 3 bedroom, 2 bathroom home presents a chance to enjoy the vibrant lifestyle of downtown Winter Garden's golf cart district, complete with a new roof and a water heater less than two years old. A spacious driveway and manicured front lawn create a welcoming first impression. Inside, the home features a functional layout designed with both comfort and entertaining in mind. The dining area sits just off the entry and connects directly to the kitchen, making everything from casual dinners to larger gatherings feel seamless. The kitchen combines practicality with charm, featuring stainless steel appliances, built-in shelving, high ceilings, and a bright atmosphere. Overlooking the living room, it keeps the main living spaces connected while adding convenience to everyday life.The living room serves as a cozy gathering space centered around a functioning wood-burning fireplace, creating the perfect setting for relaxing evenings at home. A thoughtful split-bedroom layout provides added privacy, with the primary suite positioned separately from the secondary bedrooms. The primary bedroom includes direct access to the oversized screened-in patio and a private en suite bathroom featuring a tub and separate shower. The additional bedrooms are generously sized with natural light and ample storage, providing comfortable accommodations for family members, guests, or a home office. Step outside and enjoy an oversized screened-in patio complete with a ceiling fan, giving you the ideal place to relax outdoors while staying protected from Florida's elements and pests. Beyond the patio, the large fenced backyard provides plenty of room for four-legged friends, and little ones to roam freely without worry, or to accommodate fun activities like gardening or hosting loved ones. The options are limitless! A dedicated shed adds additional outdoor storage for tools, bikes, and recreational gear. Another standout benefit is the extremely low HOA, with the current HOA paid through June 2027, giving the next owner even more value and peace of mind. Living within Winter Garden's golf cart district means you can easily enjoy the area's beloved farmers market, boutique shopping, local restaurants, community festivals, and events without having to go far. Major highways are also conveniently nearby, along with excellent schools. With a new roof, newer water heater, spacious outdoor living areas, and an unbeatable downtown Winter Garden location, this home presents an exciting opportunity to create a space that truly reflects your style and vision. Come see the possibilities, make this home your own, and start enjoying the Winter Garden lifestyle today. Schedule your private tour!

217 Harbor Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakglen Estates SubDv. ⋅ 34787 Zip Code

Located in the Oakglen Estates community of Winter Garden, this spacious 4-bedroom, 3-bathroom home offers a functional open layout, tall ceilings and plenty of room to live and entertain. The updated kitchen features an oversized island, abundant cabinetry and a large pantry conveniently connected to the laundry room, which also provides exterior access. Luxury vinyl flooring runs throughout the main living areas, with brand-new carpet in two guest bedrooms. The spacious primary suite features additional closet/shelving, two walk-in closets and a large en-suite bathroom with a soaking tub and separate shower stall. Both guest bathrooms have been beautifully remodeled. Step outside to enjoy a private fenced backyard with a built-in sunshade, exterior electric perimeter dog fence and a variety of fruit trees, including guava and berry bushes. The home offers the space, updates and functionality today's buyers are looking for, all within a well-established Winter Garden neighborhood. Enjoy easy access to Winter Garden's Historic Downtown, Lake Apopka, the West Orange Trail for biking and walking, shopping, dining and the many amenities that make Winter Garden such a sought-after place to call home. Homes in this established community don't come to market often—don't miss your opportunity to make 531 Hearthglen Blvd your own.

531 Hearthglen Boulevard, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Winding Bay Ph 3 SubDv. ⋅ 34787 Zip Code

A RARE FIND IN THE HIGHLY DESIRABLE WINDING BAY COMMUNITY! This beautifully designed home offers the perfect blend of comfort, flexibility, and income potential. One of its most impressive features is the FULLY EQUIPPED PRIVATE ONE-BEDROOM APARTMENT ABOVE THE GARAGE with its own private entrance, spacious living room, full kitchen, private bedroom, walk-in closet, laundry area, and full bathroom. The apartment is CURRENTLY TENANT-OCCUPIED, providing immediate rental income for the next owner while also offering incredible flexibility as a guest suite, multigenerational living space, or a completely private home office. The main residence features 4 spacious bedrooms and 2.5 bathrooms, with the PRIMARY SUITE CONVENIENTLY LOCATED ON THE FIRST FLOOR, offering comfort and privacy. The open-concept floor plan showcases elegant tile flooring throughout the main living areas, premium carpeting upstairs, 8-foot interior doors, upgraded lighting, and abundant natural light that creates a warm and inviting atmosphere. A standout architectural feature is the CHARMING SECOND-FLOOR FRONT PORCH, the perfect place to enjoy your morning coffee, unwind in the evenings, or simply relax while taking in the peaceful neighborhood views. Residents of Winding Bay enjoy resort-style amenities, including a community pool, splash pad, playground, and dog park, all with a low HOA fee. Ideally located just minutes from SR-429, approximately 10 minutes from Walt Disney World, and close to Horizon West Town Center, shopping, dining, and Orlando International Airport, this home is also zoned for highly rated schools. Whether you're looking for a primary residence with built-in rental income, a home designed for multigenerational living, or the convenience of a private apartment for guests or a dedicated workspace, this exceptional property truly offers the best of Central Florida living.

15068 Lebeau Loop, Winter Garden

6 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 34787 Zip Code

TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home. Video https://youtu.be/FU5ZvzJ_3PM

16945 W Phil C Peters Road, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

NEWLY UPDATED LAMINATE FLOORING THROUGHOUT THE MAIN AREAS, BEDROOMS, AND STAIRS!!!! kITCHEN AND BATHROOMS HAVE CERAMIC TILE!!!! This amazing ready to move in 2 bed / 2 bath condo in the pristine gated community of Southern Pines with a lot of amenities. Located in the heart of charming Winter Garden and only 15 miles to Orlando. Condo Includes: 1 car GARAGE - Bonus room which is attached to living room, Walk-in closets in both bedrooms and In-unit laundry closet. Community Features Include: Water, internet, exterior & community maintenance included, amenities: Oversized Swimming pool and gazebo lounge areas - Spa / Hot Tub, Fully equipped fitness center with attached playroom, Indoor Basketball Court & Racquetball Court, Outdoor Pickleball / Tennis Court & Beach Volleyball Court, Covered Playground, Outdoor Kitchen including charcoal grills, mini fridge, sink & vending machines, Carwash station, Easy to access mailboxes at front of the community. Schedule your showing today.

417 Southern Pecan Circle Unit 201, Winter Garden

5 Beds ⋅ 6 Baths ⋅ Waterleigh Ph 1 SubDv. ⋅ 34787 Zip Code

Virtually Staged. BEST PRICED LAKEFRONT HOME in Winter Garden! Spectacular Views with 99 Feet of Shoreline! Start Enjoying LIFE ON THE LAKE in this Special Home built with the HIGHEST LEVEL OF UPGRADES! Enter this 4,641 sq ft Home with 5 Bedroom Suites and 6 Full Baths through a PRIVATE COURTYARD. Double Doors with Leaded Glass Welcome you to a life of LUXURY! First Floor has Soaring 12 Foot Ceilings, Tray Ceilings, 7 ¼” Baseboards and four Ten Foot Tall Sliders that open to the nearly HALF ACRE Premium Lot with Wide Open Lake Views! Build a DOCK and enjoy Boating, Fishing, Kayaking or try the WATER SKI COURSE on 420 Acre Lake Hickorynut just minutes from DISNEY! Outstanding Features include: Premium Lot that is over 200 Feet Deep, a true GOURMET Kitchen with all WOLF Appliances: Sub-Zero 36” SS Refrigerator, Sub-Zero 36” SS Freezer, Wolf E Series Wall Oven, Convection Steam Oven, Warming Drawer and Wolf Induction Cooktop. The DOUBLE Stacked Raised Panel Cabinetry features a HIDDEN Pantry with CUSTOM Shelving! The Great Room has a Custom Built-In and a Butler Pantry was added near the Dining Room. Oversized Covered Patio is enhanced with Electronic RETRACTABLE Screens, and the Pool Bath is just steps away. Impressive FIRST FLOOR PRIMARY SUITE with Hickory Flooring opens to Spa Bath with DOUBLE Vanities, FREESTANDING TUB, Spacious Shower and Large WALK-IN CUSTOM Closet PLUS a LAUNDRY ROOM with Sink and a STORAGE Closet! Private Suite 2 has Lake Views, Custom Built-In Shelving, Large Bath and Custom Closet. Private Suite 5 overlooks the Courtyard. The CUSTOM Staircase with Oak treads leads upstairs to 2 more Bedroom Suites with 10’ ceilings and Custom Closets, a LARGE Bonus Space wired for SURROUND SOUND is an Ideal THEATER ROOM and a large Covered Balcony with Electronic Screens that is a perfect spot for Relaxing while Enjoying the Sunset over the Lake! Upstairs Laundry Room with original plumbing has been converted to Mini Kitchen – great opportunity for a Mother-In-Law Suite! Outstanding Upgrades Include Engineered Hickory Flooring in entire 2nd Floor and Bedrooms, WATER FILTRATION system, Gutters, Drop Zone with Cabinetry, SOLID CORE Doors throughout home and UV Light in AC Units. Property is very ENERGY EFFICIENT with Double Pane Lo E Windows, Radiant Barrier and Extra Insulation in the Concrete Block. Waterleigh is a Lifestyle Community with 4 Community Pools, 3 Clubhouses with Fitness Centers, Tennis, Pickleball, Mini Golf, Parks, Playgrounds, Community Fishing Dock and MORE! HOA Does all Yard Maintenance. Schools Include Panther Lake Elementary, Water Spring Middle and NEW Horizon High School. Close to Shopping, Dining, NEW Publix, DISNEY and convenient to 429, 1-4 and 417!

8750 Bayview Crossing Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Stone Crk SubDv. ⋅ 34787 Zip Code

Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.

15187 Harrowgate Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Woodbridge On Green SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule and also yard lawncare, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.

14050 Fairway Willow Lane, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Lake Star At Ovation Phase 1b SubDv. ⋅ 34787 Zip Code

Stunning single-story luxury residence located in the highly desirable Lake Star at Ovation community in Winter Garden. Built in 2025 by M/I Homes, this expansive home offers over 4,700 sqft of heated living space with 5 bedrooms and 4.5 bathrooms, designed with a modern open-concept layout and high-end finishes throughout. The home features a spacious 3-car garage plus additional storage space, providing both functionality and convenience. The gourmet kitchen includes built-in appliances such as a cooktop, wall oven, microwave, dishwasher, range hood, and wine refrigerator, complemented by elegant stone countertops and a large island ideal for entertaining. Situated on a premium corner homesite, the property offers exceptional privacy with scenic pond views from both the backyard and side of the home. The backyard overlooks tranquil water followed by a conservation area and an additional lake beyond the tree line, creating a layered natural backdrop that ensures long-term privacy with no future construction directly behind the property. From the backyard and main living areas, residents can also enjoy seasonal views of the Disney fireworks in the distance. Located in one of Horizon West’s fastest-growing communities, close to top-rated Water Spring schools, Hamlin Town Center, major highways, and Walt Disney World, this home presents a rare opportunity to own a newer luxury residence with privacy, views, and an exceptional location. Private showings by appointment only. Please contact the listing agent directly to schedule a tour.

16788 Muskgrass Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code

Welcome to Winter Garden, which has been ranked by Money Magazine "Best Places To Live In America" and is a finalist for Hallmark Channel's 2026 "Merriest Christmas Towns" Contest. This exceptional property in the heart of the highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. Priced to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. A large shed, rated as a detached garage, provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. The 3/4 acre property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. SELLER WILL CONSIDER SUB-DIVIDINGTHE LOTS. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

205 Surprise Drive, Winter Garden

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1146 Prado Lane, Oakland

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